108534-47-0

Basic information

• Product Name: 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&
• Synonyms: 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&;4-(t-Butyldimethylsilyloxy)Phenol;4-[tert-butyl(dimethyl)silyl]oxyphenol;4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenol
• CAS NO: 108534-47-0
• Molecular Formula: C₁₂H₂₀O₂Si
• Molecular Weight: 224.374
• Product Categories: Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 108534-47-0.mol
• Article Data: 31

Chemical Properties

• Melting Point: 60-64 °C(lit.)
• Boiling Point: 266.4 °C at 760 mmHg
• Flash Point: 114.9 °C
• Appearance: White to off-white/Powder
• Density: 0.974 g/cm³
• Vapor Pressure: 0.00526mmHg at 25°C
• Refractive Index: 1.49
• PKA: 10.24±0.15(Predicted)
• CAS DataBase Reference: 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&(108534-47-0)
• EPA Substance Registry System: 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&(108534-47-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 108534-47-0(Hazardous Substances Data)

Usage

Description

4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9&, also known as a silyl ether protecting group, is a chemical compound utilized in organic synthesis to protect phenolic hydroxyl groups. It features a phenol ring with a tert-butyldimethylsilyloxy group attached, which shields the hydroxyl group from unwanted reactions, enabling selective reactions at other functional groups within a molecule. 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is an essential tool for chemists in the development of new compounds across various fields.

Uses

Used in Pharmaceutical Synthesis:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is used as a protecting group in the synthesis of pharmaceuticals for the development of new drugs. The tert-butyldimethylsilyloxy group shields the phenolic hydroxyl group, allowing for selective reactions to occur at other functional groups, which is crucial for the synthesis of complex drug molecules.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is employed as a protecting group in the synthesis of agrochemicals, such as pesticides and herbicides. The protection of phenolic hydroxyl groups enables selective reactions, facilitating the development of effective and targeted agrochemicals.
Used in Natural Product Synthesis:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is used as a protecting group in the synthesis of natural products, including the development of bioactive compounds derived from plants, fungi, and other natural sources. The selective protection of phenolic hydroxyl groups allows for the synthesis of complex natural product structures with potential therapeutic applications.
Used in Organic Synthesis Research:
4-(TERT-BUTYLDIMETHYLSILYLOXY)PHENOL 9& is utilized as a protecting group in organic synthesis research to explore new reaction pathways and develop innovative synthetic methods. The selective protection of phenolic hydroxyl groups enables chemists to investigate reactions at other functional groups, leading to the discovery of new synthetic strategies and applications.

InChI:InChI=1/C12H20O2Si/c1-12(2,3)15(4,5)14-11-8-6-10(13)7-9-11/h6-9,13H,1-5H3

Upstream product

• 299917-31-0 [4-(Tetrahydropyran-2-yloxy)phenoxy]-tert-butyldimethylsilane 
• 78018-57-2 1,4-bis{[(tert-butyl)(dimethyl)silyl]oxy}benzene 
• 103-16-2 4-Benzyloxyphenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 123-31-9 hydroquinone 
• 288-32-4 1H-imidazole 
• 108534-51-6 4-((tert-butyldimethylsilyl)oxy)-4-methoxycyclohexa-2,5-dienone 
• 74293-60-0 (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 
• 108-24-7 acetic anhydride 
• 313547-95-4 (3R,4R,5R)-3-[(tert-butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone 
• 123844-15-5 [4-(Adamantan-2-ylidene-phenyl-methoxy)-phenoxy]-tert-butyl-dimethyl-silane 
• 120743-89-7 4-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-cyclohexa-2,5-dienol 

Downstream Products

• 108534-51-6 4-((tert-butyldimethylsilyl)oxy)-4-methoxycyclohexa-2,5-dienone 
• 319426-10-3 tert-butyl-[4-(3,4-dihydro-2H-pyran-2-ylmethoxy)-phenoxy]-dimethyl-silane 
• 817602-44-1 4-(tert-butyldimethylsilyloxy)phenoxycarbonyl chloride 
• 1029559-01-0 2-{[4-(tert-butyldimethylsiloxy)phenoxy]methyl}oxirane 
• 1374456-87-7 tert-butyldimethyl(4-(prop-2-yn-1-yloxy)phenoxy)silane 
• 1428556-59-5 C₁₇H₁₃Cl₂N₃O₂ 
• 1428558-21-7 5-((4-(tert-butyldimethylsilyloxy)phenoxy)methyl)-N-(3,4-dichlorophenyl)pyrimidin-2-amine 
• 1328953-37-2 4-(tert-butyldimethylsilyloxy)phenyl 3-nitrobenzenesulfonate 
• 1328953-51-0 4-(tert-butyldimethylsilyloxy)phenyl 3-aminobenzenesulfonate 
• 1072798-29-8 tert-butyl 4-(tert-butyldimethylsilyloxy)phenyl carbonate 
• 159182-39-5 [2-(4-Amino-phenyl)-ethyl]-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Isolation, synthesis, and biological activity of biphenyl and m-terphenyl-type compounds from Dictyostelium cellular slime molds

From the fruiting bodies of Dictyostelium polycephalum, we obtained four aromatic compounds: dictyobiphenyl A (1) and B (2) and dictyoterphenyl A (3) and B (4). The synthesis of 1-4 was performed to confirm the structures and obtain sufficient material fo

Efficient preparation of apically substituted diamondoid derivatives

We present an effective three-step chromatography-free sequence for the preparation of apical monohydroxy derivatives of diamantane, triamantane, and [121]tetramantane from the corresponding bis-apical diols utilizing tert-butyldimethylsilyl chloride as t

Structure-aided optimization of non-nucleoside M. tuberculosis thymidylate kinase inhibitors

Mycobacterium tuberculosis thymidylate kinase (MtTMPK) has emerged as an attractive target for rational drug design. We recently investigated new families of non-nucleoside MtTMPK inhibitors in an effort to diversify MtTMPK inhibitor chemical space. We here report a new series of MtTMPK inhibitors by combining the Topliss scheme with rational drug design approaches, fueled by two co-crystal structures of MtTMPK in complex with developed inhibitors. These efforts furnished the most potent MtTMPK inhibitors in our assay, with two analogues displaying low micromolar MIC values against H37Rv Mtb. Prepared inhibitors address new sub-sites in the MtTMPK nucleotide binding pocket, thereby offering new insights into its druggability. We studied the role of efflux pumps as well as the impact of cell wall permeabilizers for selected compounds to potentially provide an explanation for the lack of correlation between potent enzyme inhibition and whole-cell activity.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.